3-(1H-1,3-Benzimidazol-2-yl)-2,7-dimeth­oxy­quinoline

Hayette Alliouche; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah

doi:10.1107/S1600536812032357

. 2012 Jul 18;68(Pt 8):o2492. doi: 10.1107/S1600536812032357

3-(1H-1,3-Benzimidazol-2-yl)-2,7-dimethoxyquinoline

Hayette Alliouche ^a, Sofiane Bouacida ^b,^c,^*, Thierry Roisnel ^d, Ali Belfaitah ^a

PMCID: PMC3414947 PMID: 22904934

Abstract

In the title molecule, C₁₈H₁₅N₃O₂, the dihedral angle between the quinoline and benzimidazole ring systems is 23.57 (5)°. The C atoms of the methoxy groups are both close to being coplanar with their attached ring systems [deviations = 0.193 (2) and −0.020 (2) Å]. An intramolecular N—H⋯O hydrogen bond closes an S(6) ring. In the crystal, N—H⋯N hydrogen bonds link the molecules into C(4) chains propagating in [010]. Weak C—H⋯π interactions also occur.

Related literature

For our previous work on the preparation of functionalized heterocyclic compounds with potential biological activity, see: Benzerka et al. (2012 ▶); Hayour et al. (2011 ▶). For further synthetic details, see: Fioraventi et al. (2006 ▶).

Experimental

Crystal data

C₁₈H₁₅N₃O₂
M _r = 305.33
Orthorhombic,
a = 6.7094 (2) Å
b = 9.4134 (3) Å
c = 49.1620 (16) Å
V = 3104.99 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.51 × 0.29 × 0.09 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.900, T _max = 0.992
14322 measured reflections
3398 independent reflections
2696 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.112
S = 1.03
3398 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032357/hb6897sup1.cif

e-68-o2492-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032357/hb6897Isup2.hkl

e-68-o2492-Isup2.hkl^{(163.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032357/hb6897Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg4 are the centroids of the N16/N17/C15/C18/C23, N4/C3/C5/C12–C14 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N16—H16⋯N17ⁱ	0.88	2.02	2.8397 (17)	154
N16—H16⋯O2	0.88	2.27	2.7107 (17)	111
C1—H1A⋯Cg2ⁱⁱ	0.98	2.67	3.3101 (18)	123
C1—H1C⋯Cg1ⁱⁱⁱ	0.98	2.82	3.4955 (17)	127
C20—H20⋯Cg4^iv	0.95	2.99	3.8271 (18)	148

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We are grateful to all personel of the PHYSYNOR Laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are due to the MESRS (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

supplementary crystallographic information

Comment

In the course of our program related to the synthesis of new suitably functionalized heterocyclic compounds of potential biological activity, (Benzerka et al., 2012; Hayour et al., 2011), we now report herein the synthesis and structure determination of the title compound, C₁₈H₁₅N₃O₂. The reactivity of this compound and its analogues toward nucleophiles is under investigation.

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. In the asymmetric unit of title compound the dimethoxyquinoline unit bearing an benzo imidazol moiety. The two rings of quinolyl moiety are fused in an axial fashion and form a dihedral angle of 2.68 (4)°. The heterocycle ring of quinolyl unit form also with imidazol plane a dihedral angle of 24.09 (5)°. The crystal packing can be described as layers in zig zag parallel to (010) plane, along the c axis (Fig. 2). It is stabilized by intra and intermolecular hydrogen bond (N—H···N and N—H···O) and C—H···π stacking, resulting in the formation of infinite three-dimensional network linked these layers toghter and reinforcing a cohesion of structure. Hydrogen-bonding parameters are listed in table 1.

Experimental

In first, malononitrile (1.0 mmol) was condensed with 2,7-dimethoxyquinolin-3-carbaldehyde (1 mmol) to give the corresponding Knoevenagel product in 97% yield. The oxidation of this one, under mild conditions, with 2.5 eq. of m.CPBA proceeded cleany, to afford corresponding 2,2-dicyano-3-(2,7-dimethoxyquinolin-3-yl)oxirane in 64% yield, according to the method reported by Fioraventi et al. (2006) In the next step, a mixture of 1.0 mmol. of 3-(2,7-dimethoxyquinolin-3-yl)oxirane-2,2-dicarbonitrile and 1.0 eq. of o-phenylenediamine dissolved in 30 ml of anhydrous acetonitrile was refluxed during 20 h. The title compound was successfully isolated by silica gel column chromatography using n.hexane/EtOAc (3:2) mixture as eluent in good yield (62%). Colourless blocks were obtained by crystallization (slow evaporation at room temperature) from a dichloromethane/methanol solution.